5-Bromo-2-hydroxy-4'-methoxychalcone | 73110-52-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 5-Bromo-2-hydroxy-4'-methoxychalcone
• 英文别名: 3-(5-bromo-2-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 73110-52-8
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: RXEZLHKVZQYXIY-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C (decomp)
• 沸点：
  485.6±45.0 °C(Predicted)
• 密度：
  1.458±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-hydroxy-4'-methoxychalcone 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 4-bromo-2-[3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
  参考文献：
  名称：

  新型三环吡唑并[1,5- d ] [1,4]苯并a嗪-5（6 H）-one：设计，合成，模型和用作hMAO-B抑制剂

  摘要：

  基于我们最近报道的选择性hMAO-A抑制剂，分子内环化作用导致异构体选择性发生了非常有趣的变化。设计并合成了一系列具有新型三环吡唑并[1,5- d ] [1,4]苯并恶嗪-5（6 H）-支架的选择性hMAO-B抑制剂（3a - 3u）。化合物3u（IC 50  = 221 nM）表现出最佳的抑制活性和对hMAO-B的同工型选择性，优于司来吉兰（IC 50 ＝ 321nM），其是用于帕金森氏病的商业选择性hMAO-B抑制剂。模型研究表明，我们的化合物对hMAO-B的选择性取决于至少两个残基，即Ile 199和Cys 172（或对应于hMAO-A的Phe 208和Asn 181）。这些数据支持进一步的研究，以评估更有效的选择性hMAO-B抑制剂的合理设计。

  DOI：

  10.1016/j.bmc.2016.02.045
• 作为产物：
  描述：

  对甲氧基苯乙酮 、 5-溴水杨醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-Bromo-2-hydroxy-4'-methoxychalcone
  参考文献：
  名称：

  Mumtaz, Amara; Saeed, Aamer; Maalik, Aneela, Acta poloniae pharmaceutica, 2015, vol. 72, # 5, p. 937 - 941

  摘要：

  DOI：

文献信息

• Reformatsky Reaction of Methyl 1-Bromocyclopentane-1-carboxylate with 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones
  作者：E. A. Nikiforova、D. V. Baibarodskikh、N. F. Kirillov、M. V. Dmitriev、S. N. Shurov

  DOI：10.1134/s1070428019030114

  日期：2019.3

  Reformatsky reaction of methyl 1-bromocyclopentanecarboxylate with 1-aryl-3-(2-hydroxyphenyl)-prop-2-en-1-ones afforded 6-substituted 4-(2-aryl-2-oxoethyl)-2H,4H-spiro[chromene-3,1′-cyclopentan]-2-ones. A probable reaction mechanism was proposed on the basis of DFT/TZVP quantum chemical calculations.

  1-溴环戊烷甲酸甲酯与1-芳基-3-（2-羟基苯基）-丙-2-烯-1-酮的重整反应，得到6-取代的4-（2-芳基-2-氧代乙基）-2 H，4 H -螺环[chromene-3,1'-cyclopentan] -2-ones。在DFT / TZVP量子化学计算的基础上，提出了一种可能的反应机理。
• Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide with<i>o</i>-Hydroxystyrenyl Derivatives
  作者：Alati Suresh、Thekke V. Baiju、Tarun Kumar、Irishi N. N. Namboothiri

  DOI：10.1021/acs.joc.8b03039

  日期：2019.3.15

  expedient one-pot protocol for the synthesis of functionalized benzofuran containing fused and spiro-heterocycles has been accomplished by the modified Hauser–Kraus (HK) annulation of sulfonylphthalide with o-hydroxychalcones and o-hydroxynitrostyrylisoxazoles. The multicascade process involves Michael addition, Dieckmann cyclization, and a series of cyclizations, eliminations, and rearrangements to deliver

  简便的一锅法合成含有稠合和螺杂环的官能化苯并呋喃的方法是，通过磺化邻苯二甲酰的邻位羟基查耳酮和邻位羟基硝基苯乙烯基恶唑修饰的Hauser-Kraus（HK）环化反应来完成。多级联过程涉及迈克尔加成，狄克曼环化以及一系列环化，消除和重排，以提供稠合的和螺杂环的产物。稠合的茚并呋喃向萘醌（一种经典的HK加合物）的不寻常转化，揭示了合成不对称萘醌的新途径。
• Amino-substituted flavans useful as anti-viral agents
  申请人：——

  公开号：US04461907A1

  公开（公告）日：1984-07-24

  Novel compounds of formula (IID) ##STR1## wherein either both X and Y represent groups independently selected from amino and lower alkylamino, or one of X and Y represents a group selected from amino and lower alkylamino and the other of X and Y represents a hydrogen atom have been found to be active against rhinoviruses and other viruses. Processes for producing these compounds include reduction of flavanone derivatives or of flavenes. Alternatively, reductive cyclization of chalcones affords the compounds. These may also be prepared by condensation of o-(substituted methyl)phenols with styrene derivatives. Pharmaceutical formulations and methods for the administration of the compounds are described.

  式(IID)的新化合物已被发现对鼻病毒和其他病毒具有活性，其中X和Y中的一个表示从氨基和较低的烷基氨基中独立选择的基团，或者X和Y中的一个表示从氨基和较低的烷基氨基中选择的基团，而另一个表示氢原子。制备这些化合物的方法包括还原黄酮酮衍生物或黄素。另外，还可以通过还原环化的查尔酮来获得这些化合物。这些化合物还可以通过o-(取代甲基)苯酚与苯乙烯衍生物的缩合反应制备。还描述了制药配方和化合物的管理方法。
• Synthesis, biological evaluation of novel 4,5-dihydro-2H-pyrazole 2-hydroxyphenyl derivatives as BRAF inhibitors
  作者：Jia-Jia Liu、Hui Zhang、Juan Sun、Zhong-Chang Wang、Yu-Shun Yang、Dong-Dong Li、Fei Zhang、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.08.020

  日期：2012.10

  A series of novel 4,5-dihydropyrazole derivatives (3a-3t) containing hydroxyphenyl moiety as potential V600E mutant BRAF kinase (BRAF(V600E)) inhibitors were designed and synthesized. Docking simulation was performed to insert compounds 3d (1-(5-(5-chloro-2-hydroxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) and 3m (1-(3-(4-chlorophenyl)-5-(3,5-dibromo-2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) into the crystal structure of BRAF(V600E) to determine the probable binding model, respectively. Based on the preliminary results, compound 3d and 3m with potent inhibitory activity in tumor growth may be a potential anticancer agent. Results of the bioassays against BRAF(V600E), MCF-7 human breast cancer cell line and WM266.4 human melanoma cell line all showed several compounds had potent activities IC50 value in low micromolar range, among them, compound 3d and compound 3m showed strong potent anticancer activity, which were proved by that 3d: IC50 = 1.31 mu M for MCF-7 and IC50 = 0.45 mu M for WM266.5, IC50 = 0.22 mu M for BRAF(V600E), 3m: IC50 = 0.97 mu M for MCF-7 and IC50 = 0.72 mu M for WM266.5, IC50 = 0.46 mu M for BRAF(V600E), which were comparable with the positive control Erlotinib. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel tricyclic pyrazolo[1,5-d][1,4]benzoxazepin-5(6H)-one: Design, synthesis, model and use as hMAO-B inhibitors
  作者：Rui Chen、Jie Xiao、Yong Ni、Han-Fei Xu、Min Zheng、Xu Tong、Tong-Tian Zhang、Chenzhong Liao、Wen-Jian Tang

  DOI：10.1016/j.bmc.2016.02.045

  日期：2016.4

  hMAO-A inhibitors, on which, the intramolecular cyclization led to a very interesting change of isoform selectivity. A series of selective hMAO-B inhibitors (3a–3u) with novel scaffold of tricyclic pyrazolo[1,5-d][1,4]benzoxazepin-5(6H)-one were designed and synthesized. Compound 3u (IC50 = 221 nM) exhibited the best inhibitory activity and isoform selectivity against hMAO-B, superior to selegiline (IC50 = 321 nM)

  基于我们最近报道的选择性hMAO-A抑制剂，分子内环化作用导致异构体选择性发生了非常有趣的变化。设计并合成了一系列具有新型三环吡唑并[1,5- d ] [1,4]苯并恶嗪-5（6 H）-支架的选择性hMAO-B抑制剂（3a - 3u）。化合物3u（IC 50  = 221 nM）表现出最佳的抑制活性和对hMAO-B的同工型选择性，优于司来吉兰（IC 50 ＝ 321nM），其是用于帕金森氏病的商业选择性hMAO-B抑制剂。模型研究表明，我们的化合物对hMAO-B的选择性取决于至少两个残基，即Ile 199和Cys 172（或对应于hMAO-A的Phe 208和Asn 181）。这些数据支持进一步的研究，以评估更有效的选择性hMAO-B抑制剂的合理设计。